5-amino-3-oxapentyl 3,6-di-O-(α-L-rhamnopyranosyl)-α-D-mannopyranoside | 213197-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-amino-3-oxapentyl 3,6-di-O-(α-L-rhamnopyranosyl)-α-D-mannopyranoside
• CAS: 213197-58-1
• 化学式: C₂₂H₄₁NO₁₅
• 分子量: 559.565
• InChiKey: WTWIDROEYCDMRX-UVRNMODOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.52
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  252.47
• 氢给体数：
  9.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (-)-cholesterol NHS succinate 、 5-amino-3-oxapentyl 3,6-di-O-(α-L-rhamnopyranosyl)-α-D-mannopyranoside 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以59%的产率得到5-{3-[(5-cholesten-3β-yl)oxycarbonyl]propanoyl}-5-aza-3-oxapentyl 3,6-di-O-(α-L-rhamnopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Neoglycolipids Containing Oligosaccharides Based on 3,6-Branched-α-D-Mannopyranosides as the Carbohydrate Moieties

  摘要：

  Several oligosaccharides containing 3,6-branched-alpha-D-mannopyranosides were obtained by selective glycosylation of 5-azido-3-oxapentyl alpha-D-mannopyranoside with acetobromosugars. After deacetylation and reduction of the spacer azido group, the oligosaccharides were coupled with the activated hemisuccinate derivatives of cholesterol and 1,2-di-O-alkylglycerol. The neoglycolipids so obtained were characterized by NMR spectroscopy and will be used as liposome coating molecules for targeting entrapped antigens.

  DOI：

  10.1080/07328309808007460
• 作为产物：
  描述：

  2-(2-Azidoethoxy)ethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 14.0h， 生成 5-amino-3-oxapentyl 3,6-di-O-(α-L-rhamnopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Neoglycolipids Containing Oligosaccharides Based on 3,6-Branched-α-D-Mannopyranosides as the Carbohydrate Moieties

  摘要：

  Several oligosaccharides containing 3,6-branched-alpha-D-mannopyranosides were obtained by selective glycosylation of 5-azido-3-oxapentyl alpha-D-mannopyranoside with acetobromosugars. After deacetylation and reduction of the spacer azido group, the oligosaccharides were coupled with the activated hemisuccinate derivatives of cholesterol and 1,2-di-O-alkylglycerol. The neoglycolipids so obtained were characterized by NMR spectroscopy and will be used as liposome coating molecules for targeting entrapped antigens.

  DOI：

  10.1080/07328309808007460